#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230187.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230187
loop_
_publ_author_name
'Maharramov, Abel M.'
'Khalilov, Ali N.'
'Sadikhova, Nurlana D.'
'Gurbanov, Atash V.'
'Ng, Seik Weng'
_publ_section_title
;
 3-[2-Hydroxy-3-(2,4,6-trimethylphenyl)propyl]-3-methyl-1-phenylthiourea
;
_journal_coeditor_code           XU5185
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1087
_journal_paper_doi               10.1107/S1600536811012736
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H26 N2 O S'
_chemical_formula_moiety         'C20 H26 N2 O S'
_chemical_formula_sum            'C20 H26 N2 O S'
_chemical_formula_weight         342.49
_chemical_name_systematic
;
3-[2-Hydroxy-3-(2,4,6-trimethylphenyl)propyl]-3-methyl-1-phenylthiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.0400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6313(11)
_cell_length_b                   8.1579(6)
_cell_length_c                   16.4455(12)
_cell_measurement_reflns_used    4968
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1961
_cell_measurement_theta_min      2.5529
_cell_volume                     1855.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10052
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9643
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4160
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.4837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                3542
_reflns_number_total             4160
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5185.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230187
_cod_database_fobs_code          2230187
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.35275(3) 0.49063(4) 0.61941(2) 0.02172(11) Uani d . 1 . .
O O1 0.61082(7) 0.26588(12) 0.52099(7) 0.0223(2) Uani d D 1 . .
H H1 0.6434(13) 0.330(2) 0.5027(12) 0.041(6) Uiso d D 1 . .
N N1 0.51088(8) 0.30365(14) 0.65553(7) 0.0197(3) Uani d . 1 . .
N N2 0.42327(8) 0.31882(14) 0.51317(8) 0.0196(2) Uani d D 1 . .
H H2 0.4785(9) 0.292(2) 0.5069(12) 0.032(5) Uiso d D 1 . .
C C1 0.81508(10) 0.13935(16) 0.59751(10) 0.0216(3) Uani d . 1 . .
C C2 0.89199(11) 0.21843(18) 0.65953(10) 0.0260(3) Uani d . 1 . .
C C3 0.97052(11) 0.2735(2) 0.63719(12) 0.0320(4) Uani d . 1 . .
H H3 1.0215 0.3293 0.6790 0.038 Uiso calc R 1 . .
C C4 0.97654(12) 0.2495(2) 0.55560(12) 0.0340(4) Uani d . 1 . .
C C5 0.90094(12) 0.1692(2) 0.49568(11) 0.0319(4) Uani d . 1 . .
H H5 0.9043 0.1508 0.4397 0.038 Uiso calc R 1 . .
C C6 0.82014(11) 0.11434(18) 0.51461(10) 0.0254(3) Uani d . 1 . .
C C7 0.89290(13) 0.2418(2) 0.75097(11) 0.0364(4) Uani d . 1 . .
H H7A 0.9484 0.3098 0.7824 0.055 Uiso calc R 1 . .
H H7B 0.8979 0.1348 0.7792 0.055 Uiso calc R 1 . .
H H7C 0.8330 0.2961 0.7506 0.055 Uiso calc R 1 . .
C C8 1.06343(14) 0.3063(2) 0.53256(16) 0.0496(5) Uani d . 1 . .
H H8A 1.0423 0.3813 0.4834 0.074 Uiso calc R 1 . .
H H8B 1.0956 0.2112 0.5174 0.074 Uiso calc R 1 . .
H H8C 1.1087 0.3630 0.5819 0.074 Uiso calc R 1 . .
C C9 0.74118(12) 0.0268(2) 0.44548(11) 0.0327(4) Uani d . 1 . .
H H9A 0.7578 0.0233 0.3924 0.049 Uiso calc R 1 . .
H H9B 0.6800 0.0856 0.4348 0.049 Uiso calc R 1 . .
H H9C 0.7345 -0.0852 0.4643 0.049 Uiso calc R 1 . .
C C10 0.72773(10) 0.08517(17) 0.62059(10) 0.0223(3) Uani d . 1 . .
H H10A 0.7491 0.0465 0.6810 0.027 Uiso calc R 1 . .
H H10B 0.6964 -0.0080 0.5834 0.027 Uiso calc R 1 . .
C C11 0.65378(10) 0.22347(17) 0.61007(9) 0.0195(3) Uani d . 1 . .
H H11 0.6861 0.3218 0.6435 0.023 Uiso calc R 1 . .
C C12 0.57030(10) 0.16888(16) 0.64028(9) 0.0195(3) Uani d . 1 . .
H H12A 0.5280 0.0943 0.5965 0.023 Uiso calc R 1 . .
H H12B 0.5971 0.1057 0.6942 0.023 Uiso calc R 1 . .
C C13 0.54069(11) 0.36552(19) 0.74324(9) 0.0253(3) Uani d . 1 . .
H H13A 0.5239 0.4819 0.7427 0.038 Uiso calc R 1 . .
H H13B 0.6107 0.3523 0.7697 0.038 Uiso calc R 1 . .
H H13C 0.5075 0.3040 0.7765 0.038 Uiso calc R 1 . .
C C14 0.43142(10) 0.36483(16) 0.59459(9) 0.0175(3) Uani d . 1 . .
C C15 0.34745(10) 0.33743(15) 0.43473(9) 0.0177(3) Uani d . 1 . .
C C16 0.25039(10) 0.36157(17) 0.42568(10) 0.0228(3) Uani d . 1 . .
H H16 0.2307 0.3745 0.4749 0.027 Uiso calc R 1 . .
C C17 0.18274(11) 0.36650(18) 0.34365(10) 0.0274(3) Uani d . 1 . .
H H17 0.1166 0.3841 0.3374 0.033 Uiso calc R 1 . .
C C18 0.20929(11) 0.34643(19) 0.27106(10) 0.0280(3) Uani d . 1 . .
H H18 0.1619 0.3497 0.2155 0.034 Uiso calc R 1 . .
C C19 0.30580(11) 0.32148(18) 0.28011(9) 0.0251(3) Uani d . 1 . .
H H19 0.3249 0.3065 0.2307 0.030 Uiso calc R 1 . .
C C20 0.37432(10) 0.31839(16) 0.36127(9) 0.0212(3) Uani d . 1 . .
H H20 0.4405 0.3031 0.3671 0.025 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 H1 . . 114.3(14) ?
C14 N1 C13 . . 120.79(12) ?
C14 N1 C12 . . 124.00(12) ?
C13 N1 C12 . . 115.16(11) ?
C14 N2 C15 . . 131.51(12) ?
C14 N2 H2 . . 113.4(12) ?
C15 N2 H2 . . 113.7(12) ?
C6 C1 C2 . . 119.22(14) ?
C6 C1 C10 . . 121.17(13) ?
C2 C1 C10 . . 119.61(13) ?
C3 C2 C1 . . 119.47(15) ?
C3 C2 C7 . . 118.83(15) ?
C1 C2 C7 . . 121.68(14) ?
C4 C3 C2 . . 121.91(16) ?
C4 C3 H3 . . 119.0 ?
C2 C3 H3 . . 119.0 ?
C5 C4 C3 . . 117.90(15) ?
C5 C4 C8 . . 120.58(17) ?
C3 C4 C8 . . 121.51(18) ?
C4 C5 C6 . . 122.24(16) ?
C4 C5 H5 . . 118.9 ?
C6 C5 H5 . . 118.9 ?
C5 C6 C1 . . 119.24(15) ?
C5 C6 C9 . . 118.75(15) ?
C1 C6 C9 . . 122.01(14) ?
C2 C7 H7A . . 109.5 ?
C2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C4 C8 H8A . . 109.5 ?
C4 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C4 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C9 H9A . . 109.5 ?
C6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C1 C10 C11 . . 112.30(11) ?
C1 C10 H10A . . 109.1 ?
C11 C10 H10A . . 109.1 ?
C1 C10 H10B . . 109.1 ?
C11 C10 H10B . . 109.1 ?
H10A C10 H10B . . 107.9 ?
O1 C11 C12 . . 105.77(11) ?
O1 C11 C10 . . 110.52(11) ?
C12 C11 C10 . . 111.01(11) ?
O1 C11 H11 . . 109.8 ?
C12 C11 H11 . . 109.8 ?
C10 C11 H11 . . 109.8 ?
N1 C12 C11 . . 114.64(11) ?
N1 C12 H12A . . 108.6 ?
C11 C12 H12A . . 108.6 ?
N1 C12 H12B . . 108.6 ?
C11 C12 H12B . . 108.6 ?
H12A C12 H12B . . 107.6 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 N1 . . 113.87(12) ?
N2 C14 S1 . . 123.98(10) ?
N1 C14 S1 . . 122.12(10) ?
C16 C15 C20 . . 119.25(13) ?
C16 C15 N2 . . 125.74(13) ?
C20 C15 N2 . . 114.87(12) ?
C17 C16 C15 . . 119.10(14) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C18 C17 C16 . . 121.61(14) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C17 C18 C19 . . 119.26(14) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C20 C19 C18 . . 119.91(14) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 120.85(13) ?
C19 C20 H20 . . 119.6 ?
C15 C20 H20 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C14 . 1.6885(14) ?
O1 C11 . 1.4353(17) ?
O1 H1 . 0.826(9) ?
N1 C14 . 1.3583(17) ?
N1 C13 . 1.4544(18) ?
N1 C12 . 1.4730(17) ?
N2 C14 . 1.3578(18) ?
N2 C15 . 1.4086(17) ?
N2 H2 . 0.875(9) ?
C1 C6 . 1.404(2) ?
C1 C2 . 1.405(2) ?
C1 C10 . 1.5130(19) ?
C2 C3 . 1.390(2) ?
C2 C7 . 1.512(2) ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(3) ?
C4 C8 . 1.513(2) ?
C5 C6 . 1.391(2) ?
C5 H5 . 0.9500 ?
C6 C9 . 1.510(2) ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.5333(19) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.5275(19) ?
C11 H11 . 1.0000 ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C15 C16 . 1.393(2) ?
C15 C20 . 1.396(2) ?
C16 C17 . 1.389(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.380(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.386(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.3835(19) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 S1 3_666 0.830(10) 2.500(10) 3.2190(10) 146(2) yes
N2 H2 O1 . 0.880(10) 1.890(10) 2.739(2) 165(2) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.4(2) ?
C10 C1 C2 C3 . . . . -177.61(13) ?
C6 C1 C2 C7 . . . . -177.09(13) ?
C10 C1 C2 C7 . . . . 3.9(2) ?
C1 C2 C3 C4 . . . . -1.5(2) ?
C7 C2 C3 C4 . . . . 177.01(14) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
C2 C3 C4 C8 . . . . -178.50(15) ?
C3 C4 C5 C6 . . . . 0.6(2) ?
C8 C4 C5 C6 . . . . 179.65(15) ?
C4 C5 C6 C1 . . . . -0.7(2) ?
C4 C5 C6 C9 . . . . -179.63(14) ?
C2 C1 C6 C5 . . . . -0.3(2) ?
C10 C1 C6 C5 . . . . 178.68(13) ?
C2 C1 C6 C9 . . . . 178.57(13) ?
C10 C1 C6 C9 . . . . -2.4(2) ?
C6 C1 C10 C11 . . . . -94.33(16) ?
C2 C1 C10 C11 . . . . 84.66(16) ?
C1 C10 C11 O1 . . . . 67.26(15) ?
C1 C10 C11 C12 . . . . -175.70(12) ?
C14 N1 C12 C11 . . . . 90.19(16) ?
C13 N1 C12 C11 . . . . -92.18(14) ?
O1 C11 C12 N1 . . . . -76.40(14) ?
C10 C11 C12 N1 . . . . 163.70(12) ?
C15 N2 C14 N1 . . . . 170.80(13) ?
C15 N2 C14 S1 . . . . -10.8(2) ?
C13 N1 C14 N2 . . . . 167.94(12) ?
C12 N1 C14 N2 . . . . -14.56(18) ?
C13 N1 C14 S1 . . . . -10.48(18) ?
C12 N1 C14 S1 . . . . 167.02(10) ?
C14 N2 C15 C16 . . . . -22.3(2) ?
C14 N2 C15 C20 . . . . 162.14(13) ?
C20 C15 C16 C17 . . . . -0.2(2) ?
N2 C15 C16 C17 . . . . -175.56(13) ?
C15 C16 C17 C18 . . . . 0.7(2) ?
C16 C17 C18 C19 . . . . -0.3(2) ?
C17 C18 C19 C20 . . . . -0.6(2) ?
C18 C19 C20 C15 . . . . 1.1(2) ?
C16 C15 C20 C19 . . . . -0.7(2) ?
N2 C15 C20 C19 . . . . 175.19(12) ?
